5-(Azidomethyl)-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

Base Information

• Chemical Name: 5-(Azidomethyl)-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS No.: 59090-48-1
• Molecular Formula: C10H13 N5 O5
• Molecular Weight: 283.244
• NSC Number: 259913
• DSSTox Substance ID: DTXSID70974547
• Mol file: 59090-48-1.mol

Synonyms:5-azidomethyl-2'-deoxyuridine

Chemical Property of 5-(Azidomethyl)-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

Chemical Property:

• PSA: 154.30000
• LogP: -1.55964
• Solubility.: Soluble in Water, alcohols, DMSO, DMF
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 283.09166853
• Heavy Atom Count: 20
• Complexity: 500

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)CN=[N+]=[N-])CO)O

Technology Process of 5-(Azidomethyl)-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

There total 15 articles about 5-(Azidomethyl)-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

3′,5′-di-O-acetyl-5-azidomethyl-2′-deoxyuridine (72274-20-5) → 5-(azidomethyl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (59090-48-1)

Guidance literature:

With ammonium hydroxide; In 1,4-dioxane;

DOI:10.1021/ja0563657

Reference yield: 88.0%

3',5'-bis-O-(tert-butyldimethylsilyl)-5-(azidomethyl)-2'-deoxyuridine (823790-97-2) → 5-(azidomethyl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (59090-48-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1021/acs.orglett.8b03035

Reference yield: 85.0%

2'-deoxy-5-(hydroxymethyl)uridine (5116-24-5,15425-01-1,143156-50-7) → 5-(azidomethyl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (59090-48-1)

Guidance literature:

With sodium azide; In trifluoroacetic acid; at 20 ℃;

DOI:10.1016/j.tet.2013.08.069

upstream raw materials:

2'-deoxy-5-(hydroxymethyl)uridine

3′,5′-di-O-acetyl-5-azidomethyl-2′-deoxyuridine

5-(N-methoxymethylamine)-2'-deoxyuridine

3',5'-diacetylthymidine

Downstream raw materials:

5-(aminomethyl)-2'-deoxyuridine

5-(azidomethyl)-5′-O-(4,4′-dimethoxytrityl)-2′-deoxyuridine

6-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]-3,4-dihydropyrimido[4,5-d]pyrimidine-2,7(1H,6H)-dione

3'-O-(tert-butyl(dimethyl)silyl)-5'-O-(4,4'-dimethoxytrityl)-5-(azidomethyl)deoxyuridine